Notes From 20 Years of Self-Employment

I’ve been self-employed for the last two decades, and here I sit, at the same-sized desk, in the same-sized room, in the same-sized house, in the same basic sort of neighborhood. It’s pretty much been a wash, status-wise. But I’ve still signed on for a third decade of independence. It’s how I work. I don’t know any other way.

Even when I technically had a job, for much of the 90s, I still basically worked for myself. A weekly newspaper in Chicago paid me to write feature stories and do occasional half-assed but energetic political coverage. They gave me health insurance and twice-monthly paychecks, but didn’t give me a desk and didn’t want me around. When I came by, once every six weeks or so, to meet with my editor, the people who toiled daily in that dank downtown warren regarded me suspiciously, like I was a cat trying to get into the pantry. I didn’t want to trade places with them.

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It felt more like adventure than work. I lived my life according to my own rules. I could masturbate pretty much whenever I wanted.

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Most of the time, I existed in my preferred mode, sleeping past nine, drinking some tea, reading the newspaper, maybe making a couple of phone calls. The Internet hadn’t really crashed the party yet, not like now, so I’d write undistracted for a couple of hours. Then it was time for a bike ride, or some lunch, or the gym, or a long walk, or a nap, or reading a book on the couch, or maybe I’d go watch Jeopardy! at the neighborhood bar. Then night would fall. I’d go hang out at a coffeehouse for a couple of hours, or see a band, and then I’d come back to my apartment and write for a couple of hours before bed. Once a week or so, I’d do something insane like take a 20-mile, two-hour public bus trip to attend a secret laundry-workers union meeting.

It felt more like adventure than work. My deadlines got met. I got paid. And I lived my life according to my own pace, and by, mostly, my own rules. I could masturbate pretty much whenever I wanted. That was a lifelong habit I didn’t want to change.

My schedule these days is a little more regimented, but only because I’m a parent and have to run parent-related errands. I have greater responsibilities, and I have to pay for my own health insurance. So I have to make more money, to work harder. Sometimes I wake up early. Some days I need to seriously block off time to write. Occasionally I will find myself stressed and overwhelmed at all my professional responsibilities. Often, I fall asleep in front of the TV, because I am old and boring and tired. Life isn’t perfect or always easy.

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Don’t believe the motivational clickbait about making it as a self-employed person.

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But I also don’t have to commute to a suburban parking lot every day. I don’t have endless teleconference meetings. Office politics exist in my world only as occasional whispered rumors. When I’m scheduling an interview and someone asks me what my “availabilities” are, I usually say something like “I’m open all this week except Tuesday from 2 to 2:30.” Except when I’m driving carpool, my time belongs to me.

Don’t believe the motivational clickbait about making it as a self-employed person. Experts encourage people to have set hours, to incorporate, and to function, essentially, as a business. That’s not how I operate. If I worked like that, I would have quit my job years ago.

Why work at home, I figure, if you have to get ready for work? I often sit at my desk in my pajamas until long after lunchtime. When it’s hot out, I sit in only a pair or shorts, or sometimes a bathing suit. No one cares. Other than my wife and son and maybe the mailman, no one has to look at me.

Most days, I make it a goal not to shower until right before I have to leave the house. And those glorious 36-hour periods where I don’t have to leave the house at all, while rarer than they used to be, still come down the pike sometimes, gloriously and unstructured. They are the golden promise of self-employment.

But that doesn’t mean I lack professionalism. In my business dealings, I strive, and sometimes succeed, to be friendly and easy to work with. When I have to meet people in person, I clean up nice. I never miss a deadline. If I’m going to, I know it, and tell my clients long ahead of time so they can adjust. I also keep a rigid payroll accounts system, and, like all self-employed people, spend half my working hours trying to chase down checks.

If you work for yourself, you can’t be lazy, because when you stop hustling, you stop working. And you also need to be flexible about what your “work” entails. While I’ve always been a professional writer, sometimes the money comes in from book contracts. Sometimes it’s magazine and Internet stringing. I work with corporate clients, sometimes anonymously. For a few disastrous, but totally self-employed, years, I tried to make it as a TV writer in Hollywood.

But after all the schmoozing and securing of contracts, the end result is always the same: Me, at a desk in my shorts, alone in a small room, thinking my thoughts and putting them onto the computer. Sometimes the phone rings or I get emails. At times, it feels like work.